Traveling to Sag Harbor this summer? The Hamptons village is one that exudes an air of classic Americana, from its quaint Main Street lined with independently owned boutiques, to its sailboat-dotted harbors, to its wharf crowded with children eating ice cream cones with rainbow sprinkles after a long day on the boat or at Long Beach. A summer spent in Sag Harbor is likely spent the same today as it was 50 years ago.

So for those lucky enough to visit the village—yes, the former whaling port isn’t technically a town—here’s a guide on the best restaurants, shops, and places to stay.

Where to Stay

Photo: Courtesy of Baron’s Cove

Baron’s Cove—located, as the name suggests, right upon the water—embraces Sag Harbor’s nautical history: navy blue is the interior color of choice, while anchors and ropes serve as accents. Many guest rooms feature a calming harbor view, and their grounds include a tennis court and a pool. It’s also worth stopping by even if you aren’t in need of lodging. The lounge is a cozy place where a fire roars on chilly nights; on warm ones, dine outside on their deck or sit on the Adirondack chairs on their wraparound porch.

This stately Georgian hotel first opened in 1846, and, over the centuries, has become the grande dame of the town: at nights, the bar is packed with well-dressed patrons sipping martinis; during the day, townsfolk sit on the porch overlooking Main Street for lunch and people watching. There are only eight guest rooms—but arguably, there’s no more authentic stay in town.

Where to Eat

There’s no official ranking of the most critically acclaimed restaurants in the Hamptons—but if there was, Sag Harbor Tavern would arguably be at the top. From the same Michelin-starred hospitality group behind Red Hook Tavern and Saga, the cozy dockside bistro serves steaks, fish and chips, and the best burger out east.

Right upon Sag Harbor Cove is The Beacon, a waterfront restaurant where you can drink rosé and eat lobster rigatoni as the sun sets on the sailboats that stretch out into the sea. It’s a summertime staple—the restaurant is celebrating its 27th season—and, as a result, is full every night with couples, families, and celebratory singles who perch up at the bar.

On Main Street sits Page, an all-day American bistro that serves lunch, brunch, and dinner. There’s something on the menu for everyone here—dinner alone has a crowd-pleasing menu that includes caesar salads, vegetable risottos, seared tuna, and New York strips—making it an enjoyable meal made even more enjoyable by their light and airy dining room.

People travel from towns far over for Sen, the sushi restaurant that’s operated in the Hamptons for over thirty years. Come for their extensive list of speciality rolls; stay for the softshell crab steamed buns and chicken lemongrass dumplings.

There’s something simple yet elegant about the Southern Italian cuisine at Tutto il Giorni, where linguine with clams, mussels, shrimp, and penne with mozzarella are served in a quaint, rustic dining room. Although if you can—try to snag a table in their charming garden, which is adorned with greenery and hanging lanterns.

For a more social night out, Le Bibloquet is the see-and-be-seen restaurant in Sag Harbor. The bar is usually lively, especially on the weekends, when a DJ spins from a booth. As for what to order? Cajun chicken, tuna tartare, and several rounds of drinks.

There are plenty of ice cream shops in Sag Harbor. But Big Olaf Ice Cream, with its retro interiors and famous waffle cones, should satisfy your sweet tooth and your dreams of summer nostalgia.

This Sag Harbor bakery, which also has two other locations in East Hampton, was a James Beard Semi Finalist Outstanding Bakery in 2025. With every bite of a different pastry—whether it’s their monkey bread, their raisin snail, or their prosciutto Gruyère croissant—you understand why. They also have a number of breakfast and lunch offerings, like lobster rolls and chicken ban mi sandwiches.

Where to Shop

Photo: Anna Watt

“I just think our whole aesthetic just feels like the Hamptons,” TWP founder Trish Westcoat Pound says of her brand and their store in Sag Harbor, which is housed in white clapboard 18th-century home. “It’s the ease of the clothes, it’s the comfort of the clothes—it’s casual, but it’s elevated. And I think that’s what the Hamptons are.” Stop by to shop American sportswear summer staples like button-down linen shirts, light cashmere sweaters, and white jeans.

Gwyneth Paltrow’s lifestyle and wellness empire has a charming outpost in Sag Harbor that carries exactly what one m ight expect: think clean sunscreens, supplements, as well as airy linen clothing that works just as well on a boat in Sag Harbor as it does on the beaches of Malibu.

A town is only as good as its book store—and luckily, the quaint Sag Harbor Books is excellent. The tiny independent shop, which is covered in ivy, sells new and used books as well as hosts a number of author talks. (Last summer, for example, saw a meet-and-greet with Goosebumps writer R.L. Stine.)

Housed in an old barn is Sage and Madison, a charming store that sells gourmet pantry staples, locally made gift baskets, chocolates, teas, linens, and, well, a whole lot of other goods meant to liven a well-appointed home. It’s also the perfect place to shop for a hostess gift—a box of Louis Sherry chocolates is a sure way to get invited back.

See a summer blockbuster or an arthouse flick at Sag Harbor Cinema, the non-profit movie theater that’s also a historic landmark. (Its neon Art Deco sign is one of the most recognizable sits out East.)